CN102558066B - Cyanobiphenyl-functionalized benzimidazole compound, and preparation and application thereof - Google Patents

Cyanobiphenyl-functionalized benzimidazole compound, and preparation and application thereof Download PDF

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CN102558066B
CN102558066B CN201110438809.9A CN201110438809A CN102558066B CN 102558066 B CN102558066 B CN 102558066B CN 201110438809 A CN201110438809 A CN 201110438809A CN 102558066 B CN102558066 B CN 102558066B
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cyanobiphenyl
benzimidazole compound
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严锋
赵杰
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Suzhou University
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    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/542—Dye sensitized solar cells
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells
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Abstract

The invention discloses a surface decoration material of a dye-sensitized photo-anode in a dye-sensitized solar cell. The surface decoration material is a cyanobiphenyl-functionalized benzimidazole compound with a chemical structural formula shown as below, wherein, n is equal to 2 to 8. The cyanobiphenyl-functionalized benzimidazole compound is used as the photo-anode interface decoration material of the dye-sensitized solar cell; and meanwhile, under the circumstance that additives are not required in an electrolyte, the photoelectric conversion efficiency of the dye-sensitized solar cell is improved, the costs needed for manufacturing the dye-sensitized solar cell are saved and the performance of the dye-sensitized solar cell is improved.

Description

A kind of benzoglyoxaline of cyanobiphenyl functionalization and preparation thereof and application
Technical field
The invention belongs to field of dye-sensitized solar cells, relate to the face finish material of dye sensitization light anode in a kind of dye sensitization solar battery.
Background technology
Light anode is the core component of dye sensitization solar battery, and Main Function is to utilize huge surface-area to adsorb unimolecular layer dyestuff, is also the carrier of charge separation and transmission simultaneously.The semiconductor film material of applying in DSSC mainly contains TiO 2, ZnO, SnO 2, Nb 2o 5, SrTiO 3, Zn 2snO 4deng, up to the present performance is the best is still nano-TiO 2semi-conductor.But the huge surface area of semi-conducting electrode has also increased the charge recombination probability of electrode surface, thus the photoelectric transformation efficiency of reduction solar cell.In order to improve the photovoltaic performance of battery, reduce electron recombination, need to be to TiO 2electrode surface carries out passivation and protection, and in prior art, people have developed multiple physical chemistry modifying technology and improved nano-TiO 2the characteristic of electrode, for example: TiCl 4the aqueous solution is processed TiO 2light anode, at TiO 2the coated layer of material thin layer in surface, use coadsorbent, utilize the additive introduced in ionogen (referring to Chem.Rev.2010,110,6595-6663), particularly:
(1)
Figure BDA0000124438810000011
adopt TiCl 4the aqueous solution is processed TiO 2light anode, can be at the not high TiO of purity 2the coated highly purified TiO of one deck in core outside 2, increase electron injection efficiency, at semi-conductor-electrolyte interface, form blocking layer.The same with galvanic deposit, at nano-TiO 2between film, form new nano-TiO 2particle, has strengthened nano-TiO 2electrochemistry contact between particle (referring to: J.Am.Chem.Soc.1993,115,6382-6390).
(2) at nano-TiO 2surface is coated has the semi-conductor of higher conduction band position or the compound of electric charge also can be reduced in blocking layer that insulation layer forms nucleocapsid structure.TiO 2surface clading ZnO, Nb 2o 5, SrTiO 3deng battery efficiency after metal oxide be all significantly improved [Chem.Mater.2001,13,678-682; J.Phys.Chem.B, 2001,105,6347-6352; Chem.Mater.2002,13,4629-4634].Kay and
Figure BDA0000124438810000012
deng to TiO 2coated Al 2o 3, MgO, Y 2o 3after, although the photovoltage of battery and packing factor rise, short-circuit current density significantly reduces, finally caused battery efficiency reduction (referring to Chem.Mater.2002,14,2930-2935).
(3) Bongha etc. is by TiO 2surface drips certain density dendritic polyester solution coadsorbent, as the blocking layer of semi-conductor-electrolyte interface.Can effectively improve short-circuit current density, but open-circuit voltage impact is little.But polyester price used higher (3806RMB/250mg, Adrich company) (referring to: Chem.Comm.2011,47,1734-1736).Chang etc. are with pyridine fused salt as coadsorbent, and while only using niacin, open circuit voltage increases to some extent, but short-circuit current reduction is a lot, finally caused decrease in efficiency a lot, while using pyridine fused salt, owing to containing I -, efficiency is slightly increased; And, owing to being pyridine fused salt and N719 wiring solution-forming, it is very unfavorable to do like this making the cost of dye sensitization solar battery, has increased the cost of manufacture of dye sensitization solar battery (referring to Sol.Energy, 2010, doi:10.1016/j.solener.2010.10.009).
(4) Chinese invention patent that the patent No. is 200710119311.X discloses the post-decoration method of dye sensitization light anode in a kind of dye sensitization solar battery, by the nanoporous TiO preparing 2after light anode absorbing dye, then modify upper metal compound layer.Reduced TiO 2redox couple oppositely compound in injected electrons and ionogen in conduction band, has improved the photoelectric transformation efficiency of solar cell.But we can recognize reference cell placement from disclosed specification sheets, one day behind efficiency drops to 0.36% from 2.60%; The efficiency of example one drops to 3.20% from 3.22%, places and drops to two days later 1.98%.Although the rear effect of modification is better than unmodified, the stability of battery or undesirable.
In addition, in ionogen, introducing certain density additive is to reduce TiO 2an important method of electrode electron recombination (referring to: J.Am.Chem.Soc.1993,115,6382-6390; Chem.Rev.2010,110,6595-6663), and the open circuit voltage of the quality of its performance to battery, short-circuit current and dark current produce very important impact.At present, the most frequently used and the most resultful additive is that tert .-butylpyridine (TBP), N-tolimidazole (NMB), N-butyl benzoglyoxaline (NMB) are (referring to J.Am.Chem.Soc., 1993,115,6382-6390; J.Photochem.Photobiol., A 2004,162; Nature Mater, 2008,7,626); The additive of other heterocyclic also have report (referring to J.Photochem.Photobiol., A 2003,160,171; Sol.Energy Mater.Sol.Cells 2003,80,167; J.Photochem.Photobiol., A 2004,165, and 157; Sol.Energy Mater.Sol.Cells 2004,81,87; Sol.Energy Mater.Sol.Cells2005,85,333; Sol.Energy Mater.Sol.Cells 2004,82,457.).
The performance that the benzoglyoxaline that has occurred recently a kind of novel ionic liquid structure also can strengthen battery is especially stability, but increased simultaneously electrolytical viscosity (referring to Chem.Commun.2011,47,11516-11518).Guanidine class ionic liquid is also used for strengthening battery performance, but conventionally mix use with other additive (referring to: Chem.Mater.2004,16,2694-2696; J.Am.Chem.Soc., 2004,126,7164-7165; Nature Mater, 2008,7,626-630).The effect of additive is by nitrogenous heterocycle and TiO 2in conjunction with carrying out negative its energy level that moves, and then strengthen the open circuit voltage of battery, antianode carries out passivation simultaneously, stops TiO 2i in electronics and ionogen 3 -compound, improve battery efficiency.
In the ionogen of the battery of above-mentioned several method assembling, all contain certain density additive (0.45-1.0M), can reduce electrolytical specific conductivity, cause short-circuit current reduction (referring to: Electrochim.Acta 2006,51,5286-5294; Langmuir 2008,24,4411-4419; Electrochim.Acta 2010,55,7159-7165).In addition, the ionogen that some are full-bodied and solid-state, as the benzoglyoxaline of NBB, NMBI and ionic liquid structure, all can increase electrolytical viscosity (referring to Energy Mater.Sol.Cells 2007,91,1062-1065; Chem.Commun.2011,47,11516-11518), so that the rate of diffusion of reduction redox couple (referring to: Electrochim.Acta2008,53,5503-5508), cause the reduction of battery performance.Meanwhile, the cost of additive also higher (TBP:400RMB/10mL, Dalian seven-colour-light scientific & technical corporation; TBP:885RMB/25mL, NMB:646RMB/5g, NBB:212RMB/5g, Wuhan Ge Aoke teaches Instrument Ltd.).
Summary of the invention
Goal of the invention of the present invention is to provide a kind of benzimidazole compound of cyanobiphenyl functionalization, and using this light anodic interface decorative material as dye sensitization solar battery, simultaneously in the situation that ionogen does not need additive, improve the photoelectric transformation efficiency of dye sensitization solar battery, save the cost of making dye sensitization solar battery, improved the performance of dye sensitization solar battery.
To achieve the above object of the invention, the technical solution used in the present invention is: a kind of benzimidazole compound of cyanobiphenyl functionalization, and the chemical structural formula of the benzimidazole compound of described cyanobiphenyl functionalization is as follows:
Figure BDA0000124438810000031
in formula, n=2～8.
The method of preparing the benzimidazole compound of above-mentioned cyanobiphenyl functionalization comprises the following steps:
(1) with
Figure BDA0000124438810000032
for reactant, under the existence of weak base salt of wormwood, under protection of inert gas, carry out nucleophilic substitution reaction, prepare
Figure BDA0000124438810000033
(2) with
Figure BDA0000124438810000034
with benzoglyoxaline be reactant, under the existence of highly basic potassium hydroxide, under protection of inert gas, carry out nucleophilic substitution reaction, prepare
Figure BDA0000124438810000035
In technique scheme, in step (1),
Figure BDA0000124438810000041
mol ratio be 2: 1; Temperature of reaction is 60～80 ℃, and the reaction times is at least 10 hours, and the solvent of reaction is acetone;
The reaction mechanism of step (1) is as follows:
In technique scheme, in step (2),
Figure BDA0000124438810000043
the mol ratio of benzoglyoxaline and potassium hydroxide is 1: 1～1.2: 2～3; Temperature of reaction is 0-5 ℃, and the reaction times is more than 6h, and the solvent of reaction is acetonitrile;
The reaction mechanism of step (2) is as follows:
Figure BDA0000124438810000044
The benzimidazole compound of the present invention's claimed above-mentioned cyanobiphenyl functionalization of while is as the application of the light anodic interface decorative material of dye sensitization solar battery.
Adopt the benzimidazole compound of above-mentioned cyanobiphenyl functionalization as the light anodic interface decorative material of dye sensitization solar battery, to make the method for dye sensitization solar battery, specifically comprise the following steps:
(1) TiO of one deck densification is set at FTO conductive glass surface 2film: FTO conductive glass is first cleaned up, at 70 ℃ of 40mM TiCl 4in the aqueous solution, keep 30min, after taking-up with naturally drying after alcohol flushing;
(2) use blade coating technology, P25 slurry is coated with to the thick TiO of one deck 8 μ m 2film, P400 slurry is coated with the thick TiO of one deck 3 μ m 2film, calcines 30min in air at 500 ℃, when conductive glass is cooled to 80 ℃, immerses 12h in dyestuff (as Z907) solution;
(3) use H 2ptCl 6solution is coated with skim as to electrode at another piece conductive glass surface;
(4) by thermoplastic film light anode together with electrode is enclosed in, reserved aperture drips the solution of the benzimidazole compound of cyanobiphenyl functionalization on to electrode, utilize vacuum filling technology by this solution impregnation to light anode, add heat extraction solvent simultaneously, then ionogen injects by the aperture on electrode, then dresses up dye sensitization solar battery by vacuum filling technology groups.
In technique scheme, in step (4), the solvent in the solution of the benzoglyoxaline of described cyanobiphenyl functionalization is acetonitrile-methylene dichloride mixed solvent, and the concentration of solution is 0.05-0.5mol/L.
In technique scheme, in step (4), described ionogen comprises ionic liquid electrolyte and solid electrolyte, and for example, ionic liquid electrolyte is DMII/EMII/EMITCB/I 2/ NBB/GuSCN (mol ratio 12: 12: 16: 1.67: 3.33: 0.67) (referring to: Nature Mater.2008,7,626-630; Chem.Commun.2011,47,11516-11518), solid electrolyte is two fluoroform sulfimide lithiums (LiTFSI), N (PhBr 3) SbCl 6, the mixture of spiro-MeOTAD (referring to: Adv.Mater.2005,17,813-815).
Because technique scheme is used, the present invention compared with prior art has following advantages:
1. the benzoglyoxaline of cyanobiphenyl functionalization of the present invention is simple and easy to get, and cost is low, can be used as used by dye sensitization solar battery light anodic interface decorative material;
2. adopt the benzoglyoxaline of cyanobiphenyl functionalization of the present invention as modifying interface material, light anodic interface to be processed, when having avoided adding additive in ionogen, improved battery efficiency, reduced the cost of battery electrolyte;
3. when the benzoglyoxaline of employing cyanobiphenyl functionalization of the present invention is processed light anodic interface as modifying interface material, only need, to the light anode of absorption good colourant, to drip the solution of this modifying interface material, take out, by heating, volatilize and remove solvent; Battery package program is few, easily encapsulation.
Embodiment
Below in conjunction with embodiment, the invention will be further described:
Embodiment mono-:
Figure BDA0000124438810000051
synthetic: reference literature (Chem.Mater.1992,4,1246-1253), by 20mmol ethylene dibromide and 20mmol K 2cO 3join respectively 10mmol
Figure BDA0000124438810000052
acetone (20mL) solution in, N 2under protection, 70 ℃ of reaction 12h.Filter, and remove solvent and be precipitated, recrystallization obtains
Figure BDA0000124438810000053
1hNMR (300MHz, CDCl 3): 7.67 (m, 4H), 7.54 (d, 2H), 7.02 (d, 2H), 4.35 (t, 2H), 3.67 (t, 2H).Get 25mmol KOH and join 10mmol
Figure BDA0000124438810000054
in acetonitrile (20mL) solution mixing with 12mmol benzoglyoxaline, under ice-water bath, react 8h.Filtration washing obtains
Figure BDA0000124438810000055
1hNMR (300MHz, CDCCl 3): 7.90 (s, 1H), 7.82 (d, 1H), 7.60-7.70 (dd, 4H), 7.52 (d, 2H), 7.41 (d, 1H), 7.24-7.34 (m, 2H), 6.96 (d, 2H), 4.20 (t, 2H), 3.97 (dd, 2H).
Embodiment bis-
Figure BDA0000124438810000061
synthetic: reference literature (Chem.Mater.1992,4,1246-1253), by 20mmol ethylene dibromide and 20mmol K 2cO 3join respectively 10mmol
Figure BDA0000124438810000062
acetone (20mL) solution in, N 2under protection, 70 ℃ of reaction 12h.Filter, and remove solvent and be precipitated, recrystallization obtains 1hNMR (300MHz, CDCl 3): 7.66 (m, 4H), 7.53 (d, 2H), 6.99 (d, 2H), 4.06 (t, 2H), 3.51 (t, 2H), 2.10 (m, 2H), 1.98 (m, 2H).Get 25mmol KOH and join 10mmol
Figure BDA0000124438810000064
in acetonitrile (20mL) solution mixing with 12mmol benzoglyoxaline, under ice-water bath, react 8h.Filtration washing obtains 1hNMR (300MHz, CDCCl 3): 7.90 (s, 1H), 7.82 (d, 1H), (7.60-7.70 dd, 4H), 7.52 (d, 2H), (7.41 d, 1H), 7.24-7.34 (m, 2H), (6.96 d, 2H), 4.20 (t, 2H), 3.97 (dd, 2H), 2.0-2.2 (m, 2H), 1.8-1.9 (m, 2H).
Embodiment tri-
Figure BDA0000124438810000066
synthetic: reference literature (Chem.Mater.1992,4,1246-1253), by 20mmol ethylene dibromide and 20mmol K 2cO 3join respectively 10mmol
Figure BDA0000124438810000067
acetone (20mL) solution in, N 2under protection, 70 ℃ of reaction 12h.Filter, and remove solvent and be precipitated, recrystallization obtains
Figure BDA0000124438810000068
1hNMR (300MHz, CDCl 3): 7.66 (m, 4H), 7.53 (d, 2H), 6.99 (d, 2H), 4.01 (t, 2H), 3.43 (t, 2H), 1.91 (m, 2H), 1.83 (m, 2H), 1.53 (s, 4H).Get 25mmol KOH and join 10mmol
Figure BDA0000124438810000069
in acetonitrile (20mL) solution mixing with 12mmol benzoglyoxaline, under ice-water bath, react 8h.Filtration washing obtains
Figure BDA0000124438810000071
1 1hNMR (300MHz, CDCCl 3): 7.90 (s, 1H), 7.82 (d, 1H), (7.60-7.70 dd, 4H), 7.52 (d, 2H), (7.41 d, 1H), 7.24-7.34 (m, 2H), (6.96 d, 2H), 4.20 (t, 2H), 3.97 (dd, 2H), 1.72-2.02 (m, 4H), 0.9-1.6 (m, 8H).
Comparing embodiment one:
By the ionic liquid electrolyte of reporting at present, be DMII/EMII/EMITCB/I 2/ NBB/GuSCN (12: 12: 16: 1.67: 3.33: 0.67) is assembled into dye sensitization solar battery.Under room temperature environment, use xenon lamp simulated solar irradiation, light intensity 100mW/cm 2under condition, record battery (useful area 0.16cm 2) photoelectric parameter is shown in appendix (table 1).
Embodiment tetra-to nine is for adopting the benzimidazole compound of cyanobiphenyl functionalization to make the embodiment of dye sensitization solar battery as the light anodic interface decorative material of dye sensitization solar battery, and the exemplary ionic liquid electrolyte of employing is DMII/EMII/EMITCB/I 2/ NBB/GuSCN (12: 12: 16: 1.67: 3.33: 0.67) (referring to: Nature Mater.2008,7,626-630; Chem.Commun.2011,47,11516-11518), body ionogen be spiro-MeOTAD (referring to Adv.Mater.2005,17,813-815).
The making of dye sensitization solar battery is with reference to Thin solid films, 2008,516,4613-4619; J.Mater.Chem.2011,21,7326-7330; Specifically comprise the following steps:
(1) FTO conductive glass is first cleaned up, at 70 ℃ of 40mM TiCl 4in the aqueous solution, keep 30min, after taking-up, with naturally drying after alcohol flushing, at FTO conductive glass surface, form the TiO of one deck densification 2mould;
(2) use blade coating technology, with P25 slurry, be coated with the thick TiO of one deck 8 μ m 2film, P400 slurry is coated with the thick TiO of one deck 3 μ m 2film, calcines 30min in air at 500 ℃, when conductive glass is cooled to 80 ℃, immerses 12h in dyestuff (as Z907) solution;
(3) use H 2ptCl 6solution is coated with skim as to electrode at another piece conductive glass surface;
(4) by thermoplastic film light anode together with electrode is enclosed in, reserved aperture drips the solution of the benzoglyoxaline of several cyanobiphenyl functionalization on to electrode, utilize vacuum filling technology by this solution impregnation to light anode, heating (60-80 ℃) is except desolventizing simultaneously, then ionogen injects by the aperture on electrode, then dresses up dye sensitization solar battery by vacuum filling technology groups.Meanwhile, the battery that does not carry out modifying interface is as reference cell.
In technique scheme, in step (4), the solvent in the solution of the benzoglyoxaline of described cyanobiphenyl functionalization is acetonitrile-methylene dichloride mixed solvent, and the concentration of solution is 0.05-0.5mol/L.
In technique scheme, in step (4), described ionogen comprises ionic liquid electrolyte and solid electrolyte, and for example, ionic liquid electrolyte is DMII/EMII/EMITCB/I 2/ NBB/GuSCN (mol ratio 12: 12: 16: 1.67: 3.33: 0.67) (referring to: Nature Mater.2008,7,626-630; Chem.Commun.2011,47,11516-11518), solid electrolyte be spiro-MeOTAD (referring to Adv.Mater.2005,17,813-815).
Embodiment tetra-
By structure, be
Figure BDA0000124438810000081
compound carry out after the modification of light anodic interface, with ionic liquid electrolyte, be DMII/EMII/EMITCB/I 2/ GuSCN (12: 12: 16: 1.67: 3.33: 0.67) (additive-free NBB) is assembled into dye sensitization solar battery.Under room temperature environment, use xenon lamp simulated solar irradiation, light intensity 100mW/cm 2under condition, record battery (useful area 0.16cm 2) photoelectric parameter is shown in appendix (table 1).
Embodiment five
By structure, be
Figure BDA0000124438810000082
compound carry out after the modification of light anodic interface, with ionic liquid electrolyte, be that DMII/EMII/EMITCB/I2/GuSCN (12: 12: 16: 1.67: 3.33: 0.67) (additive-free NBB) is assembled into dye sensitization solar battery.Under room temperature environment, use xenon lamp simulated solar irradiation, light intensity 100mW/cm 2under condition, record battery (useful area 0.16cm 2) photoelectric parameter is shown in appendix (table 1).
Embodiment six
By structure, be compound carry out after the modification of light anodic interface, with ionic liquid electrolyte, be DMII/EMII/EMITCB/I 2/ GuSCN (12: 12: 16: 1.67: 3.33: 0.67) (additive-free NBB) is assembled into dye sensitization solar battery.Under room temperature environment, use xenon lamp simulated solar irradiation, light intensity 100mW/cm 2under condition, record battery (useful area 0.16cm 2) photoelectric parameter is shown in appendix (table 1).
Comparing embodiment two:
Get 0.05mL containing 4-tertiary butyl pyridine (TBP), two fluoroform sulfimide lithiums (LiTFSI), N (PhBr 3) SbCl 6, the chlorobenzene solution of spiro-MeOTAD, drips at dye sensitization TiO 2photoanode surface, after spin coating, except desolventizing, then the gold electrode that plates the about 30nm of one deck in the above form battery (Adv.Mater.2005,17,813-815).Under room temperature environment, use xenon lamp simulated solar irradiation, light intensity 100mW/cm 2under condition, record battery (useful area 0.16cm 2) photoelectric parameter is shown in appendix (table 1).
Embodiment seven
Drip several 0.1M's
Figure BDA0000124438810000091
in TiO 2on light anode, heat 80-100 ℃ and remove to solvent, then by two fluoroform sulfimide lithiums (LiTFSI), N (PhBr 3) SbCl 6, the chlorobenzene solution of spiro-MeOTAD, drips at dye sensitization TiO 2photoanode surface, after spin coating, except desolventizing, then the gold electrode that plates the about 30nm of one deck in the above form battery (Adv.Mater.2005,17,813-815).Under room temperature environment, use xenon lamp simulated solar irradiation, light intensity 100mW/cm 2under condition, record battery (useful area 0.16cm 2) photoelectric parameter is shown in appendix (table 1).
Embodiment eight
Drip several 0.1M's
Figure BDA0000124438810000092
in TiO 2on light anode, heat 80-100 ℃ and remove to solvent, then by two fluoroform sulfimide lithiums (LiTFSI), N (PhBr 3) SbCl 6, the chlorobenzene solution of spiro-MeOTAD, drips at dye sensitization TiO 2photoanode surface, after spin coating, except desolventizing, then the gold electrode that plates the about 30nm of one deck in the above form battery (Adv.Mater.2005,17,813-815).Under room temperature environment, use xenon lamp simulated solar irradiation, light intensity 100mW/cm 2under condition, record battery (useful area 0.16cm 2) photoelectric parameter is shown in appendix (table 1).
Embodiment nine
Drip several 0.1M's
Figure BDA0000124438810000093
in TiO 2on light anode, heat 80-100 ℃ and remove to solvent, then by two fluoroform sulfimide lithiums (LiTFSI), N (PhBr 3) SbCl 6, the chlorobenzene solution of spiro-MeOTAD, drips at dye sensitization TiO 2photoanode surface, after spin coating, except desolventizing, then the gold electrode that plates the about 30nm of one deck in the above form battery (Adv.Mater.2005,17,813-815).Under room temperature environment, use xenon lamp simulated solar irradiation, light intensity 100mW/cm 2under condition, record battery (useful area 0.16cm 2) photoelectric parameter is shown in appendix (table 1).
Table 1
Figure BDA0000124438810000101
Note: test condition: room temperature environment, is used xenon lamp simulated solar irradiation, light intensity 100mW/cm 2under condition, record battery (useful area 0.16cm 2).
Wherein,
Figure BDA0000124438810000102
represent to there is peak power output (P when battery max) time, corresponding electric current and the product of voltage and the ratio of short-circuit current and open circuit voltage product.Electricity conversion calculates and adopts following formula: η = { V × J } max P in × 100 % = V oc × J sc × FF P in × 100 % .

Claims (5)

1. a benzimidazole compound for cyanobiphenyl functionalization, is characterized in that, the chemical structural formula of the benzimidazole compound of described cyanobiphenyl functionalization is as follows: in formula, n=2～8.
2. the preparation method of the benzimidazole compound of cyanobiphenyl functionalization described in claim 1, is characterized in that, comprises the following steps:
(1) with for reactant, under the existence of weak base salt of wormwood, under protection of inert gas, carry out nucleophilic substitution reaction, prepare
Figure FDA0000124438800000013
(2) with
Figure FDA0000124438800000014
with benzoglyoxaline be reactant, under the existence of highly basic potassium hydroxide, under protection of inert gas, carry out nucleophilic substitution reaction, prepare
3. the preparation method of the benzimidazole compound of cyanobiphenyl functionalization according to claim 2, is characterized in that, in step (1),
Figure FDA0000124438800000016
mol ratio be 2: 1; Temperature of reaction is 60～80 ℃, and the reaction times is at least 10 hours, and the solvent of reaction is acetone.
4. the preparation method of the benzimidazole compound of cyanobiphenyl functionalization according to claim 2, is characterized in that, in step (2),
Figure FDA0000124438800000017
the mol ratio of benzoglyoxaline and potassium hydroxide is 1: 1～1.2: 2～3; Temperature of reaction is 0-5 ℃, and the reaction times is more than 6h, and the solvent of reaction is acetonitrile.
Described in claim 1 benzimidazole compound of cyanobiphenyl functionalization as the application of the light anodic interface decorative material of dye sensitization solar battery.
CN201110438809.9A 2011-12-23 2011-12-23 Cyanobiphenyl-functionalized benzimidazole compound, and preparation and application thereof Expired - Fee Related CN102558066B (en)

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